Total synthesis of a series of thiazolinone and thiazolidinone analogues of the antibacterial oxazolinone antibiotic indolmycin is described. The synthetic route involves nucleophilic displacement of mesyloxy and chloro groups from methyl 2-substituted-3-(indol-3-yl) propionates 3 and 4 and butyrate 19 with N-substituted thioureas. The formation of the rearranged chloro esters 29, 43, and 44 from@(RS, RS)-methyl indolmycenate (27), a (RS ...
